JP2774926B2 - Skin protection composition - Google Patents

Abstract

Cosmetic or dermopharmaceutic composition. This composition is characterised in that it contains, in a suitable vehicle, an antioxidising system of synergistic action consisting of the combination of a lysine, histidine or arginine lauroylmethionate and of at least one polyphenol chosen from: a) a derivative of 2,5-dihydroxyphenylcarboxylic acid, a homologue or a corresponding salt, b) an ester or amide of caffeic acid, c) a flavonoid or an extract based on flavonoids, d) an extract of rosemary containing diphenols, and their mixtures. The use of the antioxidising system allows good conservation for the compositions containing fatty substances which are sensitive to oxidation.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a basic amino acid, lauroylmethionate.
te) (i.e., the N- lauroyl Meteor Nin basic amino acid addition salts), containing said set alignment to have a synergistic effect to a combination of at least one polyphenol as an antioxidant, a lipid skin Protects against oxidation
For protecting the skin .

[0002]

To protect the skin, such as BACKGROUND OF THE INVENTION invention is to provide a majority of the cosmetic composition and dermatological compositions
Because of the composition consists of fatty phase, the oily substance has a tendency to Dosan of extent also at room temperature. As a result of this oxidation,
The properties of the composition, especially the odor
s) changes significantly, rendering the composition unusable after a period of time.

[0003] In order to protect the composition against these oxidation phenomena, it is customary to incorporate a protective agent acting as an antioxidant.

[0004] Among the most commonly used antioxidant compounds, mention may be made of ascorbic acid, which acts in particular by directly absorbing oxygen, but ascorbic acid is very poorly soluble in fats. As a result, the composition cannot be sufficiently protected.

In order to overcome the difficulties of ascorbic acid,
Recently, various antioxidant systems
In particular, French Patent Application No. 90 11384 (Patent No. 2,666,809)
No.) is proposed in the specification. The antioxidant system comprises at least one tocopherol or tocopherol derivative and at least one non-thiolated polypeptide.

Similarly, French Patent Application No. 88 10295 (Patent No. 2,634,779) discloses that tocopherol or a mixture of tocopherols, or one of caffeic acid or a derivative thereof and at least one complexing agent It has been proposed to use an antioxidant system consisting of at least one non-thiolated polypeptide.

[0007] Although these antioxidant systems have a particularly pronounced synergistic effect, they nonetheless tend to cause storage problems during prolonged storage.

If the antioxidants described above are effective for the good preservation of fats in skin-protecting compositions, the compositions may in certain applications be subject to the action of peroxides, especially air pollutants or ultraviolet light. Can effectively remove the deleterious effects of the organic peroxide formed by the organic peroxide.

Living cells have a variety of natural means for lipid peroxides, especially epidermal glutathione peroxidase, but the detoxifying efficacy of the epidermal glutathione peroxidase is greatly reduced under the influence of UV exposure.

[0010] Therefore, it is irreversible
It is important to have an antioxidant that can prevent the formation of free radicals (free radicals) that are responsible for the oxidative phenomena that can cause cell damage.

[0011]

SUMMARY OF THE INVENTION After conducting various studies on a number of substances, a skin-protecting composition containing easily oxidizable fats (corps glas) was successfully improved. Both storable and, in addition, efficiently protecting skin lipids by using a synergistic antioxidant system consisting of the basic amino acid lauroyl methionate and at least one polyphenol. allowing the resulting Rukoto is surprisingly been found by the present inventors.

Therefore, according to the gist of the present invention, ricin,
Lauroyl methionate of histidine or arginine and the following polyphenols: a) (2,5-dihydroxyphenyl) carboxylic acid derivative, homologue or corresponding salt thereof; b) caffeic acid ester or caffeic acid amide; c) flavonoid; Or an extract containing flavonoids, d) mannen wax containing diphenols (roma
rin) extract, and that Do contained in a suitable vehicle the antioxidant system having a synergistic effect an antioxidant system comprising a combination of at least one polyphenol chosen from mixtures thereof Characterized by the fact that the skin
Provided is a skin-protecting composition for protecting lipids from oxidation .

Among the aforementioned lauroyl methionates, particularly preferred for use according to the invention are Giva
L-lysine lauroyl methionate (MW = 477.7) sold by udan Lavirotte.

The above (2,5-dihydroxyphenyl) carboxylic acid derivatives, homologues and salts thereof are known compounds, and they are particularly known from French Patent Application No. 78.24174 (Patent No. 2,
No. 400,358) and No. 78.24175 (Patent No. 2,400,359)
No.) is described in the specification.

These (2,5-dihydroxyphenyl) carboxylic acid derivatives have the following general formula (I): Wherein R ₁ represents a group OR ₄ , OH or —N (r ′) (r ″),
R ₄ is substituted with a linear or branched (C ₁ -C ₂₀ ) alkyl group, a linear or branched (C ₂ -C ₂₀ ) alkenyl group, or one or more hydroxyl or alkoxy groups (C ₁
ＣC ₂₀ ) alkyl, wherein r ′ and r ″ are the same or different and are a hydrogen atom, (C ₁ -C ₂₀ )
Alkyl group, or represents (C ₂ ~C ₆₎ hydroxyalkyl group or a (C ₃ ~C ₆₎ polyhydroxyalkyl group,
Alternatively, r ′ and r ″ together form a heterocycle with the nitrogen atom, m is 1 or 2, and (i) when m is 1, of the radicals R ₂ and R ₃ At least one of them represents a linear or branched (C ₁ -C ₄ ) alkyl group, the other optionally represents a hydrogen atom, and (ii) when m is 2, R ₂ and R ₃ are the same. A hydrogen atom or a linear or branched chain (C ₁ to
C ₄ ) represents an alkyl group].

Among the particularly preferred compounds represented by the general formula (I), methyl 2,5-dihydroxy-4-methyl-phenylacetate can be particularly mentioned.

Among the above-mentioned caffeic acid esters, in particular, the following formula (II): [Wherein, Z represents a (C ₁ -C ₈ ) alkyl group or a phytol residue].

Among the above-mentioned caffeic acid amides, in particular, the following formula (III): [Wherein, Z ′ is a (C ₁ -C ₈ ) alkyl group, particularly (C ₆
To C ₈ ) alkyl group].

The compound represented by the above formula (II) or (III) is known and can be prepared according to a known method.

Among the flavonoids, the following two general formulas, ie, the following general formula (IV): Wherein A ″, B ″, C ″ and D ″ each independently represent H or OH; E ″ represents H, OH or OX ′ (where X ′ represents the following group: F ″, G ″ and J ″ each independently represent H or OH; and X ₁ represents —CH ₂ —,
-CO- or -CHOH-, provided that at least two of the radicals A "to G" or J "represent OH or that the radical E" represents OX '], and The following general formula (V): Wherein A ′, C ′ and D ′ independently represent H, OH or OCH ₃ ; E ′ is H, OH or OR ′ (where R ′ is a sugar represented by the formula R′OH B ′, F ′, G ′ and J ′ each independently represent H, OH, OCH ₃ or —OCH ₂ —CH ₂ —OH, provided that the groups A ′ to At least two of G 'or J' are OH
Flavonoids].

Among the above-mentioned sugars R'OH, rutinose can be mentioned.

The compound represented by the above formula (IV) or (V) is known. These compounds are, inter alia, Harborne JB,
Mabry TJ, Helga Mabry, "The Flavonoids", published in 1975, pages 1-45.

Among the above flavonoids which can be used according to the invention, in particular taxifolin, catechin, epicatechin, eriodictyol, naringenin, rutin, troxerutin, chrysin, tangeretin (tan)
geretine), luteolin, epigallocatechin, epigallocatechin gallate, quercetin, fizetin, kaempferol, galangin, gallocatechin and epicatechin gallate.

Such compounds are particularly described by Nikko in "Sunp
Henon is present in the green tea extract sold under the name.

The extract of mannen wax which can be used according to the invention is characterized in that it contains l'acide carnosique and carnosol, which extract is extracted, for example, from mannen wax and then distilled (Ch
ang et al., JOSC, Vol. 61, No. 6, issued June 1984)
Or Europe as described in Patent Application EP 307,626, for the purpose of removing odorous substances, or by extraction with a polar solvent such as ethanol and then extracted with a nonpolar solvent such as hexane, extracted with either I can do it.

Carnosic acid and carnosol correspond to the following formula:

In the skin-protecting composition of the present invention, the lysine, histidine or arginine lauroyl methionate is generally used in an amount of 0.5% based on the total weight of the composition.
It is present at a concentration between 02% and 5%.

The polyphenol is present in a proportion of 0.005 to 5% by weight based on the total weight of the composition.
The ratio of the basic amino acid lauroyl methionate to the polyphenol is generally between 20/80 and 90/10.

When the polyphenol is a (2,5-dihydroxyphenyl) carboxylic acid derivative represented by the general formula (I), the derivative is present in an amount of 0.05 to 1% by weight based on the total weight of the composition. It is preferred to be present at a concentration of

When the polyphenol is caffeic acid ester or caffeic amide, its concentration is preferably 0.05 to 2% by weight based on the total weight of the composition.

Furthermore, if flavonoids or extracts containing flavonoids are used, they are generally present in a concentration of from 0.1 to 5% by weight, based on the total weight of the composition.

Similarly, if a mannen wax extract containing carnosic acid and carnosol is used, the mannen wax extract is generally present in a concentration of 0.1 to 5% by weight, based on the total weight of the composition. .

The compositions according to the invention can be of a very variable nature, in particular at least one fat which is susceptible to oxidation, in various proportions, preferably 1 to 99% by weight. It is particularly preferred that the composition contains a proportion.

The fats present in the compositions according to the invention are, for example, fats of animal origin, such as cetine (whale wax), beeswax,
Lanolin, perhydrosqualane, sea turtle oil, etc .;
Vegetable fats in the form of oils, fats or waxes, such as almond oil, avocado oil, olive oil, sesame oil or macadamia oil; optionally hydrogenated coconut or palm kernel oil, cocoa butter, carnauba wax or montan wax; and glycerol or glycol Synthetic oils comprising esters and / or ethers, such as French Patent Application No. 7
No. 5.24656 (Patent No. 2,281,916), No. 75.24657 (Patent No. 2,281,743) and No. 75.24658 (Patent No. 2,2
No. 81,744).

The skin-protecting composition of the present invention may also contain oxidizable compounds such as vitamin F or β-carotene in addition to some oxidizable fats.

The skin-protecting compositions according to the invention can be used, in particular, in the form of oily solutions, water-in-oil emulsions, oil-in-water emulsions, optionally anhydrous solid substances, lotions, fine dispersions or vesicle dispersions. Provided in form. The lipid constituting the vesicle may be of an ionic or non-ionic type, or a mixture thereof. Further, the composition for skin protection of the present invention,
Emulsions for skin care, creams [face (face) cream, hand cream, body cream, sun cream, makeup remover cream, foundation cream], liquid foundation, makeup remover, bath oil, lipstick, eye shadow, deodorant stick, etc. It can be provided in the form of

For topical application, the skin-protecting composition of the invention comprises, for example, the ingredients necessary to enable the composition to be present in a salve, cream, emulsion, ointment or oily solution, together with a vehicle. And

According to a preferred embodiment, the skin-protecting composition according to the invention is in a form intended for topical application,
In particular, it is provided in the form of a cream intended to protect skin lipids from oxidation.

The skin-protecting composition of the present invention may further contain various standard additives such as surfactants, dyes, fragrances, astringent substances, ultraviolet light absorbing substances and organic solvents as additional components.

The skin-protecting composition of the present invention is produced according to a conventional method.

[0041]

Examples The skin-protecting composition of the present invention is described by the following examples. Example 1: Moisture cream %-Lysine lauroyl methionate 1.15-2.5-Methyl dihydroxy-4-methyl-phenylacetate 1.0-Mg lanolate 3.0-Lanolin alcohol 5. 0-paraffin oil 27.0-paraffin jelly 15.0-methyl p-hydroxybenzoate 0.2-propyl p-hydroxybenzoate 0.1-deionized water The amount required to bring the total amount to 100%.

Example 2: Protective cream %-Lysine lauroyl methionate 1.3-Quercetin 0.5-Mannen wax extract 1.0-Self-emulsifying glyceryl stearate 3.0-Cetyl alcohol 0.5-Stearyl alcohol 0.5-Paraffin oil 12.0-Sesame oil 10.0- Stearic acid 3.0-Methyl p-hydroxybenzoate 0.2-Propyl p-hydroxybenzoate 0.1-Fragrance 0.3-Deionized water Required to bring the total amount to 100%

Example 3: Moisture cream for protection %-Lysine lauroyl methionate 2.3-Flavonoid extract from green tea ("Sunphenon" from Jan Dekker Inc.) 1.0-Glyceryl stearate 3.0-Stearyl alcohol 0.5- Stearic acid 2.0-Perhydrosqualane 12.0-Volatile silicone oil 5.0-Methyl p-hydroxybenzoate 0.2-Propyl p-hydroxybenzoate 0.1-Fragrance 0.3-Deionized water Amount required to bring the total to 100%

Example 4: Protective cream % for hands- Lysine lauroyl methionate 0.345-Methyl caffeate 0.4-Rutin 0.5-Sorbitan monostearate 2.0 polyoxyethylenated with 20 moles of ethylene oxide 2.0-Cetyl alcohol 1.0-Myristin Isopropyl acid 3.0-Paraffin oil 7.0-Volatile silicone oil 7.0-Methyl p-hydroxybenzoate 0.2-Propyl p-hydroxybenzoate 0.1-Deionized water Amount required to bring the total amount to 100%

Example 5: Vesicle dispersion %-Lysine lauroyl methionate 0.23-Methyl 2,5-dihydroxy-4-methyl-phenylacetate 0.05-Hydrogenated soybean lecithin 1.8-Cholesterol 0.9-Collagen palmitoyl lipased (lipacide palmitoyl) 0.3-Glycerol 0.3-Macadamia oil 15.0-Volatile silicone oil 10.0-Carboxyvinyl polymer sold by Gddorich under the name "Carbopol 940" 0.6-Methyl p-hydroxybenzoate 0.2-Triethanolamine Amount needed to reach pH = 6-Deionized water Amount needed to bring the total volume to 100%

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI A61K 31/22 A61K 31/22 31/35 31/35 35/78 35/78 C C09K 15/08 C09K 15/08 15/20 15/20 15/34 15/34

Claims (16)

(57) [Claims] 1. Lauroyl methionate of lysine, histidine or arginine and the following polyphenols: a) (2,5-dihydroxyphenyl) carboxylic acid derivative, homologue or corresponding salt, b) caffeic acid ester or caffeine An antioxidant system comprising a combination with at least one polyphenol selected from acid amide, c) a flavonoid or an extract containing flavonoids, d) a mannen wax extract containing diphenols, and a mixture thereof. coercive characterized by containing a suitable vehicle in antioxidant system having a synergistic effect Te, the skin lipids from oxidation
A composition for protecting the skin . 2. A composition of claim 1 wherein said antioxidant system is one that contains a lysine Lauro Irume isethionate. 3. The (2.5-dihydroxyphenyl)
The carboxylic acid derivative is Wherein R ₁ is a group OR ₄ , OH or —N (r ′)
R ₄ represents a linear or branched (C ₁ -C ₂₀ ) alkyl group, a linear or branched (C ₂ -C ₂₀ ) alkenyl group, or one or more hydroxyl or alkoxy groups Represents a (C ₁ -C ₂₀ ) alkyl group substituted by: wherein r ′ and r ″ are the same or different,
Hydrogen atom, (C ₁ -C ₂₀ ) alkyl group, (C _2-
Represents a C ₆ ) hydroxyalkyl group or a (C ₃ -C ₆ ) polyhydroxyalkyl group, or r ′ and r ″
Together form a heterocycle with the nitrogen atom, m is 1 or 2, and (i) when m is 1, at least one of the radicals R ₂ and R ₃ is linear or branched A chain (C ₁ -C ₄ ) alkyl group, the other optionally a hydrogen atom, and (ii) when m is 2, R ₂ and R ₃ are the same or different. Te, hydrogen atom or a linear or branched (C 1 _{-C 4)} the composition of claim 1, wherein corresponds to an alkyl group]. 4. The (2,5-dihydroxyphenyl)
A composition according to claim 1 or 3 carboxylic acid derivative is 2,5-dihydroxy-4-methylcyclohexyl phenylacetate. 5. The method of claim 1, wherein the caffeic acid ester has the formula: [Wherein, Z is (C 1 _{-C 8)} alkyl group or phytol residue] The composition of claim 1, wherein corresponds to. 6. The method of claim 1, wherein the caffeamide is of the formula: Wherein, Z 'is (C 1 _{-C 8)} alkyl group] The composition of claim 1, wherein corresponds to. 7. The method according to claim 1, wherein the flavonoid is one of the following two formulas: Wherein A ″, B ″, C ″ and D ″ independently represent H or OH, respectively; E ″ is H, OH or OX ′ (where X ′ is the following group: F ", G" and J "are each independently H or O
H represents X; and X ₁ represents —CH ₂ —, —CO— or —C
Represents HOH—, provided that at least two of the radicals A ″ to G ″ or J ″ represent OH, or the radical E ″
Represents OX ′], and the following formula (V): Wherein, A ', C' and D 'represent each H, OH or OCH ₃ independently of one another; E' is H, OH or OR '(where, R' is a sugar of formula R'OH B ′, F ′, G ′ and J ′ each independently represent H, OH, OCH ₃ or —OCH ₂ —CH ₂ —OH, provided that the groups A ′ to 'at least two of or J' G composition of claim 1, wherein which corresponds to one of a condition that represents OH]. Wherein said lysine, histidine or arginine Lauro Irume composition 請 Motomeko 1 wherein that isethionate is be present in a concentration of 0.02% to 5% relative to the total weight of said composition. 9. 請 <br/> Motomeko 1 composition, wherein the polyphenol is you present in a concentration of 0.005 to 5% by weight relative to the total weight of said composition. Wherein said claim 1 (2,5-dihydroxyphenyl) carboxylic acid derivative is present at a concentration of 0.05 to 1% by weight relative to the total weight of the composition, 3 or
5. The composition according to 4 . 11. The method according to claim 11, wherein the caffeic acid ester and / or caffeic acid amide is present in an amount of 0.0
The composition according to claim 1, 5 or 6 , which is present in a concentration of from 5 to 2% by weight. 12. The flavonoid or flavonoid-containing extract may be contained in an amount of 0.1% to the total weight of the composition.
The composition of claim 1 which is present in a concentration of 5 wt%. 13. The extract of mannen wax containing l'acid carnosique and carnosol and present at a concentration of 0.1 to 5% by weight based on the total weight of the composition. The composition of claim 1 . 14. At least one of the fats susceptible to oxidation
Seeds, composition according to any one of 請 Motomeko 1-13 you in a proportion of 1 to 99% by weight relative to the total weight of said composition. 15. Vitamin F or β- composition according to any one of 請 Motomeko 1-14 you containing <br/> at least one oxidizing susceptible compound selected from carotene. 16. surfactants, dyes, perfumes, astringents material, any one of 請 Motomeko 1-15 that further to contain various additives selected from UV absorbing agent and an organic solvent as an additional component A composition according to claim 1.